For a first date, things were going fairly well. We were at Megu, a pricey Japanese restaurant in Midtown Manhattan, eating perfectly cooked Kobe beef. My companion, a wealthy finance type, was telling me all about himself and posing questions that suggested he was interested in me. Then, matter-of-factly, he said, “Whether I met you on the site or at the Standard, you’d cost me at least 10 grand a month.”
The site he was referring to was Seeking Arrangement, an online network that pairs people possessing resources (“sugar daddies” and “sugar mommies”) with those, usually much younger, seeking them (“sugar babies”). I had become a member a few weeks earlier, partly as a social experiment and partly out of genuine desperation. I was frustrated with my job, which offered little upward mobility, and was thinking about quitting it to pursue my goal of becoming a full-time freelance writer. Holding me back were my lack of savings and my fear of sacrificing a regular paycheck. If I had a hefty allowance from a generous benefactor, though, I figured that I could take the leap comfortably.
The idea of wealthy older people supporting struggling younger ones is nothing revolutionary, after all—look what Peggy Guggenheim did for Jackson Pollock or the Tuohys did for N.F.L. star Michael Oher. So what if I had to tap into my inner geisha to secure a patron?